What Happened When We Tried a Luxury Matchmaking Service

In our digital time, where dating has a “try anything, no boundaries” approach, the thought of a matchmaker somehow seems scarier and more intimidating than having someone simply swipe right. But when the opportunity to try my hand at the age-old method of courtship came my way, I decided to swallow my fear and carpe diem.

I was lucky enough to be introduced to Emily Hahn from LastFirst (see what she did there?) and her unconventional matchmaking background—she previously worked for Ralph Lauren in Paris and first came into matchmaking from her ability to make personal connections. Her philosophy to dating calmed my nerves enough to take the plunge.

The first step was to meet Emily in person—she has a full team that meets with each LastFirst member. After telling her a bit more about myself and letting her get a feel for what I was like and what I was looking for came the hard part: my questionnaire.

Full disclosure: I usually crush a questionnaire! I like to think I know myself pretty well and also have the ability to answer tough questions honestly and openly. This part of the process actually proved to be the most valuable and taught me the most.

Like most people, I was in a pattern and kept on dating the same type of guy only to be surprised when they all ended the same way. The questions I had to answer forced me to take a look at what I really wanted for myself and how I saw my life in the future. After realizing what I was truly looking for (stability, potential family) it dawned on me that I was perhaps more conventional than I thought I was. Answering these personal questions allowed me to step back and not only see the mistakes I was making, but also gave me the opportunity to acknowledge the things that I wanted but perhaps was not fully admitting to myself.

I went on two lovely dates that Emily set up, and the whole process was so smooth and eye-opening it’s something I would recommend to anyone. I came to think of a matchmaker as being set up by a friend—it’s a trusted source with your best interests in mind. In the age where the dating landscape changes almost daily, maybe there’s something to be said for the most tried-and-true methods.